Private charter · MDW → PSF
Chicago to Pittsfield
742 miles. One price for the whole airplane.
Price your flight from Chicago to Pittsfield
The trip
Chicago to Pittsfield, door to door faster.
Trade about 16 hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Pittsfield Municipal Airport in Pittsfield, 742 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.
- Distance
- 742 mi
- Flight
- —
- Driving
- 16 hours
- Passengers
- Up to 1
Departing Chicago
Airports in Chicago
MDW
Major airportChicago Midway International Airport
Chicago · KMDW
- From downtown
- 9 mi
- Longest runway
- 6,522 ft
ORD
Major airportChicago O'Hare International Airport
Chicago · KORD
- From downtown
- 16 mi
- Longest runway
- 13,000 ft
PWK
Commercial airportChicago Executive Airport
Chicago/Prospect Heights/Wheeling · KPWK
- From downtown
- 21 mi
- Longest runway
- 5,001 ft
GYY
Commercial airportGary/Chicago International Airport
Gary · KGYY
- From downtown
- 21 mi
- Longest runway
- 8,859 ft
Arriving Pittsfield
Airports in Pittsfield
PSF
Regional airportPittsfield Municipal Airport
Pittsfield · KPSF
- From downtown
- 3 mi
- Longest runway
- 5,792 ft
HCC
Regional airportColumbia County Airport
Hudson
- From downtown
- 26 mi
- Longest runway
- 5,350 ft
When you land
Things to do in Pittsfield
Pittsfield is the largest city in Berkshire County and the practical center of the Berkshires, a region of wooded hills, lakes and small towns that has drawn summer residents from New York and Boston for well over a century. The city grew up around General Electric’s transformer and plastics operations, and today its economy relies on healthcare, plastics and defense manufacturing, and a cultural sector that includes the Colonial Theatre and the Berkshire Museum. Lenox, home of Tanglewood, and Stockbridge are a short drive south.
- 01
Tanglewood
In Lenox, the summer home of the Boston Symphony Orchestra presents concerts in the open-sided Koussevitzky Music Shed and Seiji Ozawa Hall, with picnickers spread across the lawn.
- 02
Hancock Shaker Village
Just west of downtown, this living history museum preserves a former Shaker community, including its distinctive 1826 round stone barn, working farm and collection of Shaker furniture.
- 03
The Mount
Edith Wharton designed and built this Lenox estate in 1902, and its house and formal gardens are open for tours that explore her life, writing and ideas about design.
- 04
Mass MoCA
About 20 miles north in North Adams, a vast former factory complex holds one of the largest contemporary art museums in the country, along with performances and festivals.
- 05
The Clark Art Institute
In Williamstown, the Clark pairs a fine collection of French Impressionist and American paintings with walking trails across its hillside campus and views of the surrounding mountains.
- 06
Mount Greylock State Reservation
The highest point in Massachusetts rises north of Pittsfield, with a summit road, the Veterans War Memorial Tower, the Appalachian Trail and Bascom Lodge for meals and overnight stays.
Questions
Chicago to Pittsfield flights
How long is a private flight from Chicago to Pittsfield?
About a short flight in a private jet, for 742 miles direct. Driving the same trip takes about 16 hours.
Which airports do flights from Chicago to Pittsfield use?
You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Pittsfield Municipal Airport (PSF) or Columbia County Airport (HCC). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Chicago to Pittsfield cost?
The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.
Can I book a round trip between Chicago and Pittsfield?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Pittsfield back to Chicago are priced the same way.
Return flight
Pittsfield to Chicago
More flights from Chicago
More flights to Pittsfield
Explore Chicago private charter and Pittsfield private charter, airports and things to do. Arriving at Pittsfield Municipal Airport (PSF).
Chicago to Pittsfield, on your schedule
Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.
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